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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2020-02-26 21:23:46 UTC
HMDB IDHMDB0002065
Secondary Accession Numbers
  • HMDB02065
Metabolite Identification
Common Name6-Lactoyltetrahydropterin
Description6-Lactoyltetrahydropterin is a putative intermediate in the de novo synthesis of tetrahydrobiopterin (BH4) pathway, in a reaction involving the enzyme sepiapterin reductase (E.C. 1.1.1.153) in human liver. In brain, an enzyme distinct from sepiapterin reductase catalyzes the TPNH-dependent reduction of 6-pyruvoyl-tetrahydropterin to 6-lactoyl-tetrahydropterin. (PMID: 4004850 ). In brain, the expression of other enzymes involved in BH4 biosynthesis includes aldose reductase, carbonyl reductase, GTP-cyclohydrolase I, and 6-pyruvoyltetrahydrobiopterin. Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. (PMID: 17270157 ).
Structure
Data?1582752226
Synonyms
ValueSource
2-Amino-6-lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-oneChEBI
6-1'-oxo-2'-Hydroxypropyl tetrahydropterinChEBI
6-Lactoyl tetrahydropterinHMDB
6-Lactoyl-5,6,7,8-tetrahydropterinHMDB
Lactoyl-H4-pterinHMDB
Lactoyl-PH4HMDB
1'-oxo-2'-Hydroxypropyl-tetrahydropterinHMDB
Chemical FormulaC9H13N5O3
Average Molecular Weight239.2312
Monoisotopic Molecular Weight239.101839307
IUPAC Name2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one
Traditional Name6-lactoyl tetrahydropterin
CAS Registry Number33405-80-0
SMILES
CC(O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2
InChI Identifier
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,12,15H,2H2,1H3,(H4,10,11,13,14,17)
InChI KeyHKCYZTKHPLJZDR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Acyloin
  • Pyrimidine
  • Alpha-aminoketone
  • Heteroaromatic compound
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Ketone
  • Azacycle
  • Secondary amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP-1.6ALOGPS
logP-1.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.12ChemAxon
pKa (Strongest Basic)4.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.87 m³·mol⁻¹ChemAxon
Polarizability22.59 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2900000000-49dec0d6931d1e9bad0aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2900000000-8f1d69e548d027d65a19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0090000000-a0f9d3c66da5b6d5f581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0940000000-176c06edb35b9da14cbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-4910000000-a4fc7ca72b4b46138d0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-6c319e8337df67fc476dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1920000000-bfd50799ec0cb51b89feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdo-9200000000-fe4583b38b03564abe97Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022828
KNApSAcK IDNot Available
Chemspider ID148245
KEGG Compound IDC04244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6468
PubChem Compound169508
PDB IDNot Available
ChEBI ID17248
Food Biomarker OntologyNot Available
VMH IDHC01254
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Milstien S, Kaufman S: Biosynthesis of tetrahydrobiopterin: conversion of dihydroneopterin triphosphate to tetrahydropterin intermediates. Biochem Biophys Res Commun. 1985 May 16;128(3):1099-107. [PubMed:4004850 ]
  2. Tobin JE, Cui J, Wilk JB, Latourelle JC, Laramie JM, McKee AC, Guttman M, Karamohamed S, DeStefano AL, Myers RH: Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. Brain Res. 2007 Mar 30;1139:42-7. Epub 2007 Jan 8. [PubMed:17270157 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
P35270
Molecular weight:
28048.13
Reactions
Tetrahydrobiopterin + NADP → 6-Lactoyltetrahydropterin + NADPH + Hydrogen Iondetails
6-Lactoyltetrahydropterin + NADP → Dyspropterin + NADPH + Hydrogen Iondetails